Holiday rentals in Hillsdale

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Top-rated holiday rentals in Hillsdale

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Top guest favourite
The great room features a tall ceiling with a modern chandelier overhead. A cozy leather Chesterfield sofa surrounds a rustic coffee table. Large windows provide views of the lake, framed by warm-toned drapes. A fireplace adds warmth, complemented by vintage decor elements on the walls.
Cabin in Amery
5.0 out of 5 average rating, 151 reviews

Lakefront Cabin | Amazing Views | Kayaks Wildlife

Welcome to The Backwater, a newly built architect designed year-round getaway on Pike Lake in Amery, WI. Nestled in the back of a quiet, lilypad-filled bay teeming with wildlife, our cabin is the perfect destination for guests who appreciate original design and crave a unique experience. Our amenities are luxurious, but our attitude is chill inside our comfy, creative digs full of nostalgic, vintage vibes. Come stay and play on the bay while enjoying Polk Co.! Follow along @thebackwater_wi on IG

Top guest favourite
An aerial view captures the expansive Lake House Mansion overlooking a tranquil body of water. Lush greenery surrounds the property, and a spacious circular patio is visible, inviting gatherings outdoors. The clear blue sky complements the serene landscape, emphasizing the home's idyllic lakeside setting.
Home in Colfax
4.96 out of 5 average rating, 154 reviews

Mansion on Lake Tainter, sleeps 28, Jacuzzi tub

This stunning lakefront Mansion is perfect for family gatherings, reunions, weddings, and retreats, just 90 min from MSP airport, 45min from Eau Claire airport . Sleeps 20 in 5 private suites (3 kings, 2 queens) plus a kids’ bunk room; add 2 more bedrooms for 6-8 extra guests. Enjoy a chef’s kitchen, 8 fireplaces, enormous game room, 10 TVs, complimentary kayaks, and a pontoon rental available . Summer offers boating and fishing, winter brings cozy fires, sledding, ice fishing and snowmobiling.

Guest favourite
A spacious living area features warm knotty pine walls and a high ceiling adorned with large windows. A stone fireplace is centrally located, surrounded by comfortable seating and wood cabinetry. Sunlight filters through the windows, illuminating the inviting space.
Cabin in Cameron
4.93 out of 5 average rating, 57 reviews

Little Cottage On Prairie

Little Cottage on Prairie meant for relaxation! Located on Prairie Lake & Lake Chetek. Launch your boat off Wolf's Den Resort or public launch. Fish Panfish, Bass, Northern, Walleye right off cabin dock. Prairie Lake water quality is great. Knotty pine interior is tastefully decorated. Relax in front of wood burning fireplace after ice fishing or snowmobiling. Stroll down to the lake. Use kayaks of boat dock. Stargaze, roast S'mores at lake-side fire pit or the fire pit closer to the cabin.

Guest favourite
A spacious yard features a mix of pink and red seating arranged around a fire pit, surrounded by trees. The house is visible in the background, showcasing a blend of brick and wood elements with large windows that invite natural light.
Home in Rice Lake
4.84 out of 5 average rating, 111 reviews

Lake Front Home on Rice Lake: Spacious 4 Bedroom

There's something here for everyone to enjoy at this 2700 sq. ft. house. A great swimming area, a dock for boats and fishing, or attractions and activities throughout the area! This 4 bedroom, 2.5 bath lake home has all of the comforts of home with a fully-equipped kitchen, cozy furnishings, free WI-FI, a laundry, and is pet friendly. With access to the lake right outside your door. No matter the season, this home is the perfect hub for outdoor adventures: hiking, ATV's, snowmobiles, and more!

Top guest favourite
Home in Chetek
5.0 out of 5 average rating, 29 reviews

Reel Therapy Retreat on Pokegama Lake in Chetek WI

Reel Therapy Retreat is your lake-life escape on Pokegama Lake in Chetek, Wisconsin’s Chain of Lakes. This spacious, family-friendly home welcomes anglers, couples, crafters, hunters, and reunion crews. Wake to loon calls, launch a pontoon from the dock, kayak with the kids, or wander into town for tiki bars, cafes, and fun shops. Evenings bring glowing sunsets, crackling fires, fast Wi-Fi, modern comforts, and cozy fireplaces. Reel in peace, play, and five-star memories—then plan your return.

Guest favourite
Cabin in Almena
4.96 out of 5 average rating, 45 reviews

Lakefront Cabin · Dock · Kayaks · King BD ·Sunsets

Welcome to Sunset Cabin on Lower Turtle Lake! Outside, only steps from the water, this lakeside cabin offers a private dock, kayaks, a spacious yard, and firepit—not to mention beautiful sunsets. Inside, it comfortably sleeps 10, making it ideal for families and groups. Plan a summer fishing trip, a getaway with friends, or a trip to enjoy the many snowmobile and ATV trails. *2 King beds *2 Full/Twin bunks *Washer/Dryer *Shuffleboard *Kayaks *Games Book Now or Message With Any Questions!

Guest favourite
A modern two-story home is framed by colorful autumn trees. Large windows provide a view of the surrounding nature. A spacious deck extends from the upper level, while a fire pit area with seating is positioned on the ground level. The exterior showcases a blend of wood and stone.
Home in New Auburn
4.92 out of 5 average rating, 136 reviews

Spacious Lakefront Cabin: Sauna • Kayaks • Games

Welcome to our Perk & Pete’s! Updated 5 bedroom, 3 bathroom home with 3800 sq ft inside & over 350' of lake frontage. This beautiful property sleeps up to 10 (no more allowed due to permit restrictions). It is located on a peninsula on Tenmile lake. The house includes a fire pit area, outdoor grill, sauna, deck, patio, 4 kayaks, paddle boat & dock to maximize your time outdoors. A full kitchen, 3 fireplaces, bar, shuffleboard table & foosball table to keep you entertained inside

Guest favourite
A log cabin is framed by lush greenery, with a driveway leading to two garage doors. A pathway of stones meanders through well-kept grass, while shrubs and small plants decorate the front yard. The cabin features a covered porch, creating a welcoming entrance.
Chalet in Turtle Lake
4.9 out of 5 average rating, 110 reviews

Turtle Lodge on Upper Turtle Lake

Beautiful Log Cabin 90 minutes from the Twin Cities and steps away from prime recreational/fishing lake. Enjoy the deck overlooking lake and fire pit. In the evenings, enjoy dinner on the deck, tell stories around a campfire, savor s'mores and listen to the loons. The dock is out of the lake from Oct 1st until the week before memorial weekend. Only minutes from the ATV and Snowmobile Trails. Pontoon rental not available.

Guest favourite
Two wooden Adirondack chairs are positioned in a grassy area, facing a view of trees and a wooden fence. The expansive landscape is dotted with foliage, and the sky features scattered clouds, contributing to a serene outdoor setting.
Home in Cumberland
4.88 out of 5 average rating, 90 reviews

Four Seasons of Lakefront Fun - Main House

Wonderful ranch-style retreat with a peaceful, very secluded bay of the lake with 30 acres of privacy, woods, and lake views. Luxury woods surround the property for relaxing, family time, or a great nature get away, perfect in any season. You will be welcomed by a stone gate and quarter-mile driveway lined by maples with plenty of outdoor parking available in front of the house. Only a 1.5 hour drive from the Twin Cities!

Top guest favourite
Cottage in Cameron
5.0 out of 5 average rating, 46 reviews

Little Red Cabin~Chetek Chain, Lakefront

Welcome to The Little Red Cabin on Prairie Lake! Prairie Lake is part of the Chetek Chain of Lakes covering 3,800 surface acres. This updated 1950’s cabin offers the perfect weekend getaway or a full-on family vacation. Whether you're seeking a relaxing retreat, a fishing haven, or a place to create memories with your family, the cabin is the perfect destination. So come kick back, relax, and enjoy your stay!

Guest favourite
A spacious bedroom is highlighted by a comfortable king-sized bed adorned with colorful pillows. A ledge stone fireplace is situated near large windows, allowing natural light to fill the room. A cozy seating area with a small table is also present, enhancing the overall ambiance.
Barn in Hillsdale
4.96 out of 5 average rating, 26 reviews

The Loft Suite @ The Granary

The Loft Suite @The Granary is an ultimate retreat into luxury amid the beautiful views of the grounds. Enjoy the ultra-comfortable king-sized bed, a ledge stone fireplace, and a relaxing rainfall shower. The suite includes an atrium with a kitchenette adjacent to a main king room through spacious French doors. Many unique touches of elegant country charm. Sleeps 2.

Top guest favourite
An authentic Norwegian cabin, built with hand-hewn logs, is nestled among greenery. The structure features large windows adorned with flower boxes and a welcoming porch. A backdrop of rolling hills and trees enhances the natural setting surrounding the cabin.
Farm stay in Prairie Farm
4.97 out of 5 average rating, 145 reviews

Inga's Cabin

Step back in time. This authentic Norwegian cabin tucked in a valley among rolling hills is just 70 miles east of St. Paul. Discover the beauty of nature surrounded by hardwoods, pines and birch groves. Wander trails through 30 acres of woods and established pollinator habitat. Each season creates a fresh palette for all your senses.

Popular amenities for Hillsdale holiday rentals